21. Brian's Got A Brand New Bag
Season: 8
Episode: 4
Original Air Date: November 8th, 2009 Brian gets another opportunity at a relationship when he meets a nice girl, only to arrive at her place for their first date and find out she went out on the town with someone else. Upon meeting the girl's mother, Brian begins chatting with her, and they hit it off immediately. He begins dating the woman and eventually sneaks her back to the Griffin home for some sexual pleasure, but the family sees them and begins to make fun of Brian about the advanced age of his new fling. Determined to prove that she is more than just some old woman, he invites her over to dinner with the family, where they continue to make fun of her and the situation Brian is in. Even though his new girlfriend is 50 years old, she might as well be 150 with all of her physical ailments and the way the Family Guy writers portray her in the episode. It's pretty funny to watch her unravel, and to see Brian slowly come to the realization that she isn't someone he can see himself settling down in a long-term relationship with makes for even more humorous moments. Brian simply can't find any luck with the ladies, unfortunately.